1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Quinoxaline

HRID 1961616Notes

Reaction equation

HRID 1961616 reaction equation
[CH3:1][CH2:2]N=C=NCCCN(C)C.[CH:12]1[CH:13]=[CH:14][C:15]2[N:20](O)N=[N:18][C:16]=2[CH:17]=1>CS(C)=O>[N:20]1[C:15]2[C:16](=[CH:17][CH:12]=[CH:13][CH:14]=2)[N:18]=[CH:2][CH:1]=1

Participants

4

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 7045Quinoxaline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compounds of structure H may be prepared as illustrated in Scheme 2. Reaction of a carboxylic acid E with various hydrazides in the presence of EDCI and HOBt in DMSO yields quinoxaline F. Quinoxaline F may then be treated with phosphorus oxychloride to give quinoxaline G. Subsequent reaction of quinoxaline G with ammonia at elevated temperature then provides compounds H.

Workup

  1. customCompounds of structure H may be prepared

Sources & evidence

ORD record
ord-1bd9d3816bab4169906fe9477a90f182
Source dataset
uspto-grants-2013_04
Patent number
US08415353B2

Reaction notes

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